#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:46:17 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258123 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/10/7241064.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241064
loop_
_publ_author_name
'Tervola, Essi'
'Truong, Khai-Nghi'
'Ward, Jas S.'
'Priimagi, Arri'
'Rissanen, Kari'
_publ_section_title
;
 Fluorescence enhancement of quinolines by protonation
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              29385
_journal_page_last               29393
_journal_paper_doi               10.1039/D0RA04691D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C13 H10 N, C2 Cl3 O2'
_chemical_formula_sum            'C15 H10 Cl3 N O2'
_chemical_formula_weight         342.59
_chemical_name_common            Benzoquinoline+Trichloroacetate
_chemical_name_systematic        11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.611(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.6910(2)
_cell_length_b                   24.1354(7)
_cell_length_c                   18.5026(5)
_cell_measurement_reflns_used    7316
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.508
_cell_measurement_theta_min      0.407
_cell_volume                     2984.88(15)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13612
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.360
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5345
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0747P)²+4.1538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4025
_reflns_number_total             5345
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra04691d2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7241053--7241066.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241064
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.876
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8611(4) 0.54530(12) 0.15949(15) 0.0276(6) Uani 1 1 d . . . . .
H1N H 0.860112 0.504461 0.177412 0.033 Uiso 1 1 calc R U . . .
C1A C 0.8622(4) 0.58668(14) 0.20938(18) 0.0243(7) Uani 1 1 d . . . . .
C2 C 0.8613(5) 0.55494(16) 0.08843(19) 0.0320(8) Uani 1 1 d . . . . .
H2 H 0.861235 0.524566 0.055770 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8616(5) 0.60810(16) 0.0617(2) 0.0343(8) Uani 1 1 d . . . . .
H3 H 0.861549 0.614675 0.011126 0.041 Uiso 1 1 calc R U . . .
C4 C 0.8620(5) 0.65153(16) 0.1098(2) 0.0335(8) Uani 1 1 d . . . . .
H4 H 0.861831 0.688486 0.092102 0.040 Uiso 1 1 calc R U . . .
C4A C 0.8626(5) 0.64191(14) 0.18493(19) 0.0272(7) Uani 1 1 d . . . . .
C5 C 0.8622(5) 0.68587(15) 0.2363(2) 0.0340(9) Uani 1 1 d . . . . .
H5 H 0.864172 0.723168 0.219902 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8591(5) 0.67534(16) 0.3078(2) 0.0350(9) Uani 1 1 d . . . . .
H6 H 0.857713 0.705303 0.341048 0.042 Uiso 1 1 calc R U . . .
C6A C 0.8579(5) 0.61955(15) 0.3343(2) 0.0307(8) Uani 1 1 d . . . . .
C7 C 0.8516(5) 0.60889(18) 0.4093(2) 0.0375(9) Uani 1 1 d . . . . .
H7 H 0.845671 0.639005 0.442210 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8538(6) 0.55583(19) 0.4351(2) 0.0409(10) Uani 1 1 d . . . . .
H8 H 0.850488 0.549351 0.485652 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8611(5) 0.51111(17) 0.3874(2) 0.0365(9) Uani 1 1 d . . . . .
H9 H 0.863526 0.474359 0.405850 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8648(5) 0.51980(15) 0.31416(19) 0.0299(8) Uani 1 1 d . . . . .
H10 H 0.869147 0.489021 0.282259 0.036 Uiso 1 1 calc R U . . .
C10A C 0.8620(5) 0.57413(14) 0.28588(18) 0.0266(7) Uani 1 1 d . . . . .
Cl1 Cl 0.5167(2) 0.33555(6) 0.11677(9) 0.0746(4) Uani 1 1 d . . . . .
Cl2 Cl 0.9134(2) 0.30250(5) 0.08553(8) 0.0699(4) Uani 1 1 d . . . . .
Cl3 Cl 0.8135(3) 0.32908(6) 0.23131(7) 0.0906(6) Uani 1 1 d . . . . .
O1 O 0.8445(6) 0.43743(11) 0.17962(15) 0.0610(9) Uani 1 1 d . . . . .
O2 O 0.8286(7) 0.42250(13) 0.06249(16) 0.0721(11) Uani 1 1 d . . . . .
C11 C 0.8231(6) 0.40914(15) 0.12517(19) 0.0323(8) Uani 1 1 d . . . . .
C12 C 0.7764(7) 0.34640(16) 0.1403(2) 0.0406(10) Uani 1 1 d . . . . .
N13 N 0.3703(4) 0.54818(12) 0.32938(15) 0.0261(6) Uani 1 1 d . . . . .
H13N H 0.369864 0.586556 0.354929 0.031 Uiso 1 1 calc R U . . .
C13A C 0.3633(5) 0.54661(14) 0.25527(18) 0.0249(7) Uani 1 1 d . . . . .
C14 C 0.3778(5) 0.50264(15) 0.3701(2) 0.0312(8) Uani 1 1 d . . . . .
H14 H 0.385592 0.505929 0.421305 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3743(6) 0.45062(16) 0.3387(2) 0.0364(9) Uani 1 1 d . . . . .
H15 H 0.378147 0.418271 0.367975 0.044 Uiso 1 1 calc R U . . .
C16 C 0.3651(5) 0.44644(16) 0.2649(2) 0.0372(9) Uani 1 1 d . . . . .
H16 H 0.362186 0.410900 0.242806 0.045 Uiso 1 1 calc R U . . .
C16A C 0.3599(5) 0.49448(15) 0.22128(19) 0.0302(8) Uani 1 1 d . . . . .
C17 C 0.3538(5) 0.49158(17) 0.1439(2) 0.0368(9) Uani 1 1 d . . . . .
H17 H 0.350186 0.456511 0.120543 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3530(5) 0.53838(17) 0.10396(19) 0.0343(9) Uani 1 1 d . . . . .
H18 H 0.349468 0.535643 0.052697 0.041 Uiso 1 1 calc R U . . .
C18A C 0.3574(5) 0.59169(16) 0.13675(19) 0.0305(8) Uani 1 1 d . . . . .
C19 C 0.3578(5) 0.64027(17) 0.0944(2) 0.0356(9) Uani 1 1 d . . . . .
H19 H 0.355401 0.637268 0.043167 0.043 Uiso 1 1 calc R U . . .
C20 C 0.3614(5) 0.69146(17) 0.1256(2) 0.0370(9) Uani 1 1 d . . . . .
H20 H 0.362946 0.723636 0.096021 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3629(5) 0.69683(16) 0.2010(2) 0.0355(8) Uani 1 1 d . . . . .
H21 H 0.364511 0.732649 0.222283 0.043 Uiso 1 1 calc R U . . .
C22 C 0.3621(5) 0.65044(15) 0.24449(19) 0.0295(8) Uani 1 1 d . . . . .
H22 H 0.362525 0.654463 0.295574 0.035 Uiso 1 1 calc R U . . .
C22A C 0.3607(4) 0.59719(15) 0.21356(18) 0.0262(7) Uani 1 1 d . . . . .
Cl4 Cl 0.5084(2) 0.69513(5) 0.57655(8) 0.0752(5) Uani 1 1 d . . . . .
Cl5 Cl 0.1107(2) 0.65077(5) 0.59319(6) 0.0664(4) Uani 1 1 d . . . . .
Cl6 Cl 0.17958(15) 0.72931(4) 0.48193(5) 0.0409(3) Uani 1 1 d . . . . .
O3 O 0.3508(4) 0.63513(11) 0.41477(13) 0.0378(6) Uani 1 1 d . . . . .
O4 O 0.3755(4) 0.57878(11) 0.51117(14) 0.0433(7) Uani 1 1 d . . . . .
C23 C 0.3422(5) 0.62264(15) 0.47949(18) 0.0286(8) Uani 1 1 d . . . . .
C24 C 0.2858(6) 0.67242(15) 0.5297(2) 0.0363(9) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1A 122.7(3) . . ?
C2 N1 H1N 118.6 . . ?
C1A N1 H1N 118.7 . . ?
N1 C1A C4A 118.5(3) . . ?
N1 C1A C10A 120.7(3) . . ?
C4A C1A C10A 120.8(3) . . ?
N1 C2 C3 121.1(3) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C4A 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C4A C4 H4 119.6 . . ?
C1A C4A C4 118.2(3) . . ?
C1A C4A C5 119.4(3) . . ?
C4 C4A C5 122.4(3) . . ?
C6 C5 C4A 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4A C5 H5 119.5 . . ?
C5 C6 C6A 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C6A C6 H6 119.6 . . ?
C7 C6A C10A 118.8(3) . . ?
C7 C6A C6 120.5(3) . . ?
C10A C6A C6 120.7(3) . . ?
C8 C7 C6A 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6A C7 H7 119.6 . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C10A 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C10A C10 H10 119.8 . . ?
C10 C10A C6A 119.0(3) . . ?
C10 C10A C1A 123.8(3) . . ?
C6A C10A C1A 117.2(3) . . ?
O2 C11 O1 129.6(4) . . ?
O2 C11 C12 116.3(3) . . ?
O1 C11 C12 114.1(3) . . ?
C11 C12 Cl3 112.5(3) . . ?
C11 C12 Cl2 111.4(3) . . ?
Cl3 C12 Cl2 111.0(2) . . ?
C11 C12 Cl1 107.2(3) . . ?
Cl3 C12 Cl1 107.1(2) . . ?
Cl2 C12 Cl1 107.4(2) . . ?
C14 N13 C13A 122.8(3) . . ?
C14 N13 H13N 118.6 . . ?
C13A N13 H13N 118.6 . . ?
N13 C13A C16A 118.1(3) . . ?
N13 C13A C22A 120.7(3) . . ?
C16A C13A C22A 121.2(3) . . ?
N13 C14 C15 120.8(3) . . ?
N13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C16A 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C16A C16 H16 119.7 . . ?
C13A C16A C16 118.6(3) . . ?
C13A C16A C17 119.3(3) . . ?
C16 C16A C17 122.0(3) . . ?
C18 C17 C16A 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16A C17 H17 119.8 . . ?
C17 C18 C18A 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
C18A C18 H18 119.2 . . ?
C19 C18A C18 121.0(3) . . ?
C19 C18A C22A 118.4(3) . . ?
C18 C18A C22A 120.5(3) . . ?
C20 C19 C18A 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C18A C19 H19 119.4 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C22A 120.3(3) . . ?
C21 C22 H22 119.9 . . ?
C22A C22 H22 119.9 . . ?
C22 C22A C18A 119.3(3) . . ?
C22 C22A C13A 123.7(3) . . ?
C18A C22A C13A 116.9(3) . . ?
O4 C23 O3 131.1(3) . . ?
O4 C23 C24 114.8(3) . . ?
O3 C23 C24 114.1(3) . . ?
C23 C24 Cl6 113.6(2) . . ?
C23 C24 Cl5 110.4(3) . . ?
Cl6 C24 Cl5 107.3(2) . . ?
C23 C24 Cl4 107.8(3) . . ?
Cl6 C24 Cl4 108.3(2) . . ?
Cl5 C24 Cl4 109.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.335(4) . ?
N1 C1A 1.360(4) . ?
N1 H1N 1.0400 . ?
C1A C4A 1.408(5) . ?
C1A C10A 1.447(5) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.410(5) . ?
C4 H4 0.9500 . ?
C4A C5 1.424(5) . ?
C5 C6 1.348(5) . ?
C5 H5 0.9500 . ?
C6 C6A 1.433(5) . ?
C6 H6 0.9500 . ?
C6A C7 1.414(5) . ?
C6A C10A 1.417(5) . ?
C7 C8 1.366(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C10A 1.412(5) . ?
C10 H10 0.9500 . ?
Cl1 C12 1.791(5) . ?
Cl2 C12 1.753(4) . ?
Cl3 C12 1.742(4) . ?
O1 C11 1.220(4) . ?
O2 C11 1.206(4) . ?
C11 C12 1.574(5) . ?
N13 C14 1.332(4) . ?
N13 C13A 1.370(4) . ?
N13 H13N 1.0400 . ?
C13A C16A 1.407(5) . ?
C13A C22A 1.444(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(5) . ?
C15 H15 0.9500 . ?
C16 C16A 1.412(5) . ?
C16 H16 0.9500 . ?
C16A C17 1.432(5) . ?
C17 C18 1.350(6) . ?
C17 H17 0.9500 . ?
C18 C18A 1.422(5) . ?
C18 H18 0.9500 . ?
C18A C19 1.410(5) . ?
C18A C22A 1.427(5) . ?
C19 C20 1.363(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 C22A 1.407(5) . ?
C22 H22 0.9500 . ?
Cl4 C24 1.776(4) . ?
Cl5 C24 1.775(4) . ?
Cl6 C24 1.765(4) . ?
O3 C23 1.239(4) . ?
O4 C23 1.225(4) . ?
C23 C24 1.575(5) . ?
